General Approach to the Synthesis of the Chlorosulfolipids Danicalipin A, Mytilipin A, and Malhamensilipin A in Enantioenriched Form

[Image: see text] A second-generation synthesis of three structurally related chlorosulfolipids has been developed. Key advances include highly stereocontrolled additions to α,β-dichloroaldehydes, kinetic resolutions of complex chlorinated vinyl epoxide intermediates, and Z-selective alkene cross me...

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Autores principales: Chung, Won-jin, Carlson, Joseph S., Vanderwal, Christopher D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3954434/
https://www.ncbi.nlm.nih.gov/pubmed/24494597
http://dx.doi.org/10.1021/jo5000829
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author Chung, Won-jin
Carlson, Joseph S.
Vanderwal, Christopher D.
author_facet Chung, Won-jin
Carlson, Joseph S.
Vanderwal, Christopher D.
author_sort Chung, Won-jin
collection PubMed
description [Image: see text] A second-generation synthesis of three structurally related chlorosulfolipids has been developed. Key advances include highly stereocontrolled additions to α,β-dichloroaldehydes, kinetic resolutions of complex chlorinated vinyl epoxide intermediates, and Z-selective alkene cross metatheses of cis-vinyl epoxides. This strategy facilitated the synthesis of enantioenriched danicalipin A, mytilipin A, and malhamensilipin A in nine, eight, and 11 steps, respectively.
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spelling pubmed-39544342015-02-04 General Approach to the Synthesis of the Chlorosulfolipids Danicalipin A, Mytilipin A, and Malhamensilipin A in Enantioenriched Form Chung, Won-jin Carlson, Joseph S. Vanderwal, Christopher D. J Org Chem [Image: see text] A second-generation synthesis of three structurally related chlorosulfolipids has been developed. Key advances include highly stereocontrolled additions to α,β-dichloroaldehydes, kinetic resolutions of complex chlorinated vinyl epoxide intermediates, and Z-selective alkene cross metatheses of cis-vinyl epoxides. This strategy facilitated the synthesis of enantioenriched danicalipin A, mytilipin A, and malhamensilipin A in nine, eight, and 11 steps, respectively. American Chemical Society 2014-02-04 2014-03-07 /pmc/articles/PMC3954434/ /pubmed/24494597 http://dx.doi.org/10.1021/jo5000829 Text en Copyright © 2014 American Chemical Society
spellingShingle Chung, Won-jin
Carlson, Joseph S.
Vanderwal, Christopher D.
General Approach to the Synthesis of the Chlorosulfolipids Danicalipin A, Mytilipin A, and Malhamensilipin A in Enantioenriched Form
title General Approach to the Synthesis of the Chlorosulfolipids Danicalipin A, Mytilipin A, and Malhamensilipin A in Enantioenriched Form
title_full General Approach to the Synthesis of the Chlorosulfolipids Danicalipin A, Mytilipin A, and Malhamensilipin A in Enantioenriched Form
title_fullStr General Approach to the Synthesis of the Chlorosulfolipids Danicalipin A, Mytilipin A, and Malhamensilipin A in Enantioenriched Form
title_full_unstemmed General Approach to the Synthesis of the Chlorosulfolipids Danicalipin A, Mytilipin A, and Malhamensilipin A in Enantioenriched Form
title_short General Approach to the Synthesis of the Chlorosulfolipids Danicalipin A, Mytilipin A, and Malhamensilipin A in Enantioenriched Form
title_sort general approach to the synthesis of the chlorosulfolipids danicalipin a, mytilipin a, and malhamensilipin a in enantioenriched form
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3954434/
https://www.ncbi.nlm.nih.gov/pubmed/24494597
http://dx.doi.org/10.1021/jo5000829
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